CAS 20350-15-6

Brefeldin A

Description:

Brefeldin A is a fungal metabolite originally isolated from the mold *Brefeldia maxima*. It is a potent inhibitor of protein transport from the endoplasmic reticulum to the Golgi apparatus, making it a valuable tool in cell biology research. The compound is characterized by its ability to disrupt the Golgi structure and function, leading to the accumulation of proteins in the endoplasmic reticulum. Brefeldin A has a complex structure, featuring a lactone ring and multiple functional groups that contribute to its biological activity. It is soluble in organic solvents such as dimethyl sulfoxide (DMSO) and has been shown to have effects on various cellular processes, including cell signaling and apoptosis. Additionally, Brefeldin A has been studied for its potential therapeutic applications, particularly in cancer and viral infections, due to its ability to modulate intracellular trafficking pathways. However, its use is primarily confined to laboratory settings for research purposes.

Formula: C₁₆H₂₄O₄

InChI: InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1

InChI key: InChIKey=KQNZDYYTLMIZCT-KQPMLPITSA-N

SMILES: O[C@H]/1[C@]2([C@@](C[C@H](O)C2)(/C=C/CCC[C@H](C)OC(=O)\C=C1)[H])[H]

Synonyms:

• (1R,2E,6S,10E,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
• (1R,2E,6S,10E,11aS,13S,14aR)-1,6,7,8,9,11a,12,13,14,14a-Decahydro-1,13-dihydroxy-6-methyl-4H-cyclopent[f]oxacyclotridecin-4-one
• (1R,2E,6S,10E,13S)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
• (1R,2E,6S,10E,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
• (1R,2Z,6S,11aR,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
• (1S,2E,6S,10E,11aS,13S,14aR)-1,13-dihydroxy-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
• 1,6,7,8,9,11a,12,13,14,14a-Decahydro-1,13-dihydroxy-6-methyl-4H-cyclopent [f]oxacyclotridecin-4-one
• 4H-Cyclopent[f]oxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, (1R,2E,6S,10E,11aS,13S,14aR)-
• 4H-Cyclopent[f]oxacyclotridecin-4-one, 1,6,7,8,9,11a,12,13,14,14a-decahydro-1,13-dihydroxy-6-methyl-, [1R-(1R*,2E,6S*,10E,11aS*,13S*,14aR*)]-
• 4H-Cyclopent[f]oxacyclotridecin-4-one, 1,6,7,8,9,11aβ,12,13,14,14aα-decahydro-1β,13α-dihydroxy-6β-methyl-
• Ascotoxin
• Brefeldin
• Cyanaein
• Cyanein
• Decumbin
• NSC 107456
• NSC 244390
• NSC 56310
• NSC 89671
• Nectrolide
• Synergisidin

Brefeldin A

CAS: 20350-15-6

Formula: C₁₆H₂₄O₄

Purity: 100.0%

Color and Shape: Whitish amorphous solid

Molecular weight: 280.0

Ref: 8R-CL0003

4H-​Cyclopent[f]​oxacyclotridecin-​4-​one, 1,​6,​7,​8,​9,​11a,​12,​13,​14,​14a-​decahydro-​1,​13-​dihydroxy-​6-​methyl-​, (1R,​2E,​6S,​10E,​11aS,​13S,​14aR)​-

CAS: 20350-15-6

Formula: C₁₆H₂₄O₄

Purity: 99%

Color and Shape: Solid

Molecular weight: 280.3594

Ref: IN-DA00I3TZ

Brefeldin A

CAS: 20350-15-6

Brefeldin A

Formula: C₁₆H₂₄O₄

Purity: By hplc: 99.47% (Typical Value in Batch COA)

Color and Shape: white powder

Molecular weight: 280.36g/mol

Ref: 54-BIB3042

Brefeldin A

CAS: 20350-15-6

Brefeldin A

Purity: ≥95%

Molecular weight: 280.36g/mol

Ref: 54-BUP14396

Brefeldin A

CAS: 20350-15-6

Formula: C₁₆H₂₄O₄

Purity: (HPLC) ≥ 98%

Color and Shape: White powder

Molecular weight: 280.36

Ref: 7W-GA2848

Brefeldin A

CAS: 20350-15-6

Formula: C₁₆H₂₄O₄

Purity: >98.0%(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 280.36

Ref: 3B-B3820

Brefeldin A

CAS: 20350-15-6

Brefeldin A (Cyanein) belongs to the class of macrolide antibiotics and is an ATPase inhibitor (IC50=0.2 μM).

Formula: C₁₆H₂₄O₄

Purity: 96.45% - 99.89%

Color and Shape: White Solid

Molecular weight: 280.36

Ref: TM-T6062

Brefeldin A

CAS: 20350-15-6

Inhibits protein translocation from ER to Golgi; fungal metabolite

Formula: C₁₆H₂₄O₄

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 280.36 g/mol

Ref: 3D-AB15917

Brefeldin A

Controlled Product

CAS: 20350-15-6

Applications A macrolide isolated from Penicillium brefeldianum. It affects the vesticular transport of the Golgi apparatus and induces DNA fragmentation which leads to apoptosis.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package
References Misumi, Y., et al.: J. Biol. Chem., 261 (1986), Mordente, J.A., et al.: J. Urol., 159, 275 (1998), Erokhina, M.V., et al.: Membr. Cell Biol., 12, 871 (1999), Nojiri, H., et al.: FEBS Letters, 453, 140 (1999),

Formula: C₁₆H₂₄O₄

Color and Shape: Neat

Molecular weight: 280.36

Ref: TR-B677240

Brefeldin A, 98%

CAS: 20350-15-6

Brefeldin A mediated apoptosis has been observed in human tumor cellsIt is an antibiotic used in cell culture and to inhibit protein secretion in mammalian and other eukaryotic cells by interfering with the function of the Golgi apparatus. This Thermo Scientific Chemicals brand product was original

Formula: C₁₆H₂₄O₄

Purity: 98%

Color and Shape: Crystals or powder or crystalline powder or granules, White to pale yellow

Molecular weight: 280.36

Ref: 02-J62340